Benzenepropanal → HCID 15887546, compound
Reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:16][N:15]([C:17](=[O:26])[C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=3)[CH2:14][CH2:13][N:12]2[C:27](=[O:36])[CH2:28][NH:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:7]=[CH:8][C:9]=1[Cl:10].CCN(C(C)C)C(C)C.[CH:46](=O)[CH2:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.[BH3-]C#N.[Na+]>C(CO)(F)(F)F>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:16][N:15]([C:17](=[O:26])[C:18]3[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=3)[CH2:14][CH2:13][N:12]2[C:27](=[O:36])[CH2:28][NH:29][CH:30]2[CH2:31][CH2:32][N:33]([CH2:46][CH2:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:34][CH2:35]2)[CH:7]=[CH:8][C:9]=1[Cl:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of compound 1 obtained from Example 9 (0.4 g, 0.7 mmol) in CF3CH2OH (5 mL) was added Hunig's base (0.21 g, 1.6 mmol) at 0° C. After stirring at 0° C. for 10 min, hydrocinnamaldehyde (94 mg, 0.7 mmol) was added. The reaction was stirred at 0° C. for additional 2.5 h, and NaBH3CN (100 mg, 1.6 mmol) was added. The mixture was stirred at 0° C. and gradually warmed to RT overnight. After reaction was complete, it was worked up and purified as described in Example 7 to give the title compound as a white solid, m.p. 52°-54° C.; FAB MS [M+1]+ 35 Cl 621.3.
Workup
- stirringThe reaction was stirred at 0° C. for additional 2.5 h
- stirringThe mixture was stirred at 0° C.
- temperaturegradually warmed to RT overnight
- customAfter reaction
- custompurified
Sources & evidence
- ORD record
- ord-99d2faec3ec942668474a7d270c17b77
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869488
Reaction notes
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